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Enantiospecific Synthesis of Wiedendiol-B from (−)-Sclareol and (+)-cis-Abienol

✍ Scribed by Alejandro F. Barrero; Enrique J. Alvarez-Manzaneda; Rachid Chahboun

Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
428 KB
Volume
38
Category
Article
ISSN
0040-4039

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✦ Synopsis

The fmt enantiospecificsynthesisof the cholesterolester mansferprotein (CETP)inhibitorwiedendiol-B(1) is described.The drimanicsyntbonwas prepared from(-)-sclareol( 4) and (+)-cis-abienol ( 13)by two akernativeroutes.The key steps of the reactionsequencesare the chemo-anddisstereoselectivehydrogenationof the C8-C9double bond of enal 6 and the stereoselectivecationic hydrogenationof the hydroxylgroupof 13, respectively,and the selwtive reductionof benzyl groups of 15. 01997 Elsevier Science Ltd.

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Synthesis of wiedendiol-A and wiedendiol
Synthesis of wiedendiol-A and wiedendiol-B from labdane diterpenes
✍ Alejandro F. Barrero; Enrique J. Alvarez-Manzaneda; Rachid Chahboun 📂 Article 📅 1998 🏛 Elsevier Science 🌐 French ⚖ 844 KB

Two efficient enantiospecific syntheses of wiedendioI-A (1) from (-)-sclareol (7), via I 1-bromo-8-drimene (I!) and 8-drimen-1 i-al (3), are reported. The first enantiospecific synthesis of wiedendioI-B (2), via 8S.9S-driman-! l-al (26), by two alternative mutes starting from 7 and (+)-cisabienol (8